[2-(6-((diallylamino)methyl)-benzo[1,3]dioxol-5-yl)ethylidene]((2S)-2-(methoxymethyl)pyrrolidin-1-yl)amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: [2-(6-((diallylamino)methyl)-benzo[1,3]dioxol-5-yl)ethylidene]((2S)-2-(methoxymethyl)pyrrolidin-1-yl)amine
• 英文别名: N-[[6-[(2E)-2-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]iminoethyl]-1,3-benzodioxol-5-yl]methyl]-N-prop-2-enylprop-2-en-1-amine
• 化学式: C₂₂H₃₁N₃O₃
• 分子量: 385.506
• InChiKey: AMNWVUOLPNQOGC-SVPRZPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  28
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [2-(6-((diallylamino)methyl)-benzo[1,3]dioxol-5-yl)ethylidene]((2S)-2-(methoxymethyl)pyrrolidin-1-yl)amine 、 溴乙酸甲酯 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以88%的产率得到3-(6-[(diallylamino)methyl]-benzo[1,3]dioxol-5-yl)-4-((2S)-2-(methoxymethyl)pyrrolidin-1-ylimino)butyric acid methyl ester
  参考文献：
  名称：

  Asymmetric Total Synthesis of the 1-epi-Aglycon of the Cripowellins A and B

  摘要：

  [GRAPHICS]The unusual [5.3.2]-bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellin A (1) and B (2) has been synthesized for the first time via a sequence of Sharpless dihydroxylation, ring-closing metathesis, and intramolecular Heck reaction. The asymmetric synthesis of the 1-epiaglycon 82 proceeds with virtually complete diastereo- and enantioselectivity (de, ee >= 98%) in 13 steps and an overall yield of 5.6%. In addition, three alternative approaches toward the aglycon 3 are also described focusing on (1) the alkylation of the 2-benzazepinedithianes 35 and 36 with the electrophile 11, (2) a radical cyclization of the precursor (R/S,S,S)-39, and (3) an intramolecular arylation reaction of the aryl ketone 47.

  DOI：

  10.1021/jo0518093
• 作为产物：
  描述：

  (diallyl)(6-bromobenzo[1,3]dioxol-5-ylmethyl)amine 在 正丁基锂 、 高氯酸 、 叔丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 水 为溶剂， 反应 13.0h， 生成 [2-(6-((diallylamino)methyl)-benzo[1,3]dioxol-5-yl)ethylidene]((2S)-2-(methoxymethyl)pyrrolidin-1-yl)amine
  参考文献：
  名称：

  Asymmetric Total Synthesis of the 1-epi-Aglycon of the Cripowellins A and B

  摘要：

  [GRAPHICS]The unusual [5.3.2]-bicyclic structure of the insecticidal Amaryllidaceae alkaloids cripowellin A (1) and B (2) has been synthesized for the first time via a sequence of Sharpless dihydroxylation, ring-closing metathesis, and intramolecular Heck reaction. The asymmetric synthesis of the 1-epiaglycon 82 proceeds with virtually complete diastereo- and enantioselectivity (de, ee >= 98%) in 13 steps and an overall yield of 5.6%. In addition, three alternative approaches toward the aglycon 3 are also described focusing on (1) the alkylation of the 2-benzazepinedithianes 35 and 36 with the electrophile 11, (2) a radical cyclization of the precursor (R/S,S,S)-39, and (3) an intramolecular arylation reaction of the aryl ketone 47.

  DOI：

  10.1021/jo0518093